Hydrochloric Acid → 1-Chlorononan-4-one

To the Grignard reagent prepared from a mixture of amyl bromide (226.59 g.; 1.5 moles) and magnesium (36.48 g.; 1.5 moles) in ether (1000 ml.) is added, dropwise, during one hour, 4-chlorobutyronitrile (155.34 g.; 1.5 moles). Stirring is continued for an additional one hour. The reaction mixture is poured into a mixture of finely crushed ice (1000 g.) and concentrated hydrochloric acid (750 ml.). The ether layer is separated quickly and discarded. The aqueous layer is heated on a steam bath for one hour to hydrolyze the intermediate imine and cause the separation of the ketone as an oil. After cooling, the oil is extracted with ether and the combined extracts are washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent is removed under vacuum and the residual oil is distilled to give 69.0 g. (26%) of colorless oil, b.p. 115°-117° C./14 mm.; pmr (CDCl3) δ0.090 (3H,t), 3.56 (2H,t,CH2Cl).

1. additionis added
2. waitis continued for an additional one hour
3. customThe ether layer is separated quickly
4. temperatureThe aqueous layer is heated on a steam bath for one hour
5. customthe separation of the ketone as an oil
6. temperatureAfter cooling
7. extractionthe oil is extracted with ether
8. washthe combined extracts are washed with saturated sodium chloride solution
9. dry with materialdried over anhydrous sodium sulfate
10. customThe solvent is removed under vacuum
11. distillationthe residual oil is distilled
12. customto give 69.0 g

ORD record

ord-2fa940aaf71b4ebab38dfed93ca83285

Source dataset

uspto-grants-1979_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04150235